In Chapter 20 of Mark Twain’s novel Pudd’nhead Wilson, Tom, a character born to a light-skinned black mother, has been “passing” for more than twenty years as white. He had been adopted by a wealthy judge and has recently (while dressed as a woman) murdered the judge during an attempted robbery. An Italian twin, Luigi, has been falsely arrested for the murder, and during and after Luigi’s trial (described in Chapter 20), Tom has several reasons to feel proud of himself. It seems inevitable that Luigi will be convicted of the crime, that Tom himself will escape scot free, and that Pudd’nhead Wilson, Luigi’s defense attorney, will suffer a major and very public legal defeat.

Tom, therefore, feels proud for a number of reasons, including the following:

He also feels proud of his apparent triumph over Wilson: “He left the courtroom sarcastically sorry for Wilson.”

He also feels proud that his disguise as a woman seems to have worked, and he feels proud that Wilson is unlikely ever to discover the disguise: “I'll give him a century to find her in -- a couple of them if he likes.”

He also feels proud of the fact that he has even disposed of his disguise: “the clothes that gave her her sex burnt up and the ashes thrown away -- oh, certainly, he'll find HER easy enough!”

He feels especially proud of his own general cleverness: “This reflection set him to admiring, for the hundredth time, the shrewd ingenuities by which he had insured himself against detection -- more, against even suspicion.”

He feels proud of the fact that his plan has apparently been absolutely flawless: “Nearly always in cases like this there is some little detail or other overlooked, some wee little track or trace left behind, and detection follows; but here there's not even the faintest suggestion of a trace left.”

He feels proud of his apparent intellectual superiority over the seemingly dim-witted Pudd’nhead Wilson: “The man that can track a bird through the air in the dark and find that bird is the man to track me out and find the judge's assassin -- no other need apply. And that is the job that has been laid out for poor Pudd'nhead Wilson, of all people in the world!”

He feels proud of the apparent fact that he will be able to torment Pudd’nhead about losing the case for as long as the two will know each other: "I'll never let him hear the last of that woman. Every time I catch him in company, to his dying day, I'll ask him in the guileless affectionate way that used to gravel him so when I inquired how his unborn law business was coming along, 'Got on her track yet -- hey, Pudd'nhead?'"

He feels proud of the fact that he can begin tormenting Pudd’nhead almost immediately: “He made up his mind that it would be good entertainment to look in on Wilson that night and watch him worry over his barren law case and goad him with an exasperating word or two of sympathy and commiseration now and then.”

He feels proud of the apparent fact that one of the Italian twins will pay for a crime Tom knows that he himself committed: "I owe them no good will, considering the brunet one's treatment of me that night. Prejudice or no prejudice, Pudd'nhead, I don't like them, and when they get their deserts you're not going to find me sitting on the mourner's bench."